Remote Executive Assistant to CEO | AI-Savvy & Secure

Insideoutva; South Africa; Remote; ZAR 372,000 - 465,000; Full time

Job summary

Insideoutva is seeking an Executive Assistant to be the right hand to our Founder & CEO. This remote role focuses on high-trust, precise calendar management, inbox handling, travel logistics, and day-to-day operations.

Ideal candidates have excellent English, impeccable organizational skills, and a disciplined approach to security and AI-assisted workflows, with experience supporting senior leaders in a fast-moving remote setting.

Qualifications

• 3-5+ years as Executive/Personal Assistant supporting senior leaders in a remote setting.
• Exceptional spoken and written English.
• Uncompromising security discipline for accounts, 2FA, credentials, and access boundaries.
• Systems thinking and AI fluency to streamline workflows with human oversight.
• Experience using cloud tools and productivity suites (e.g., Google Workspace, Slack, Ramp).

Responsibilities

• Executive & Personal Administrative Ownership: manage calendar, inbox, travel, and internal workflows.
• Time & Priority Management: protect focus blocks, avoid double-bookings, prepare pre-meeting materials.
• Asynchronous Execution & SOP Management: refine and maintain documentation and SOPs.
• Inbox & Voice Alignment: draft emails and communications matching CEO tone.
• Security & System Maintenance: manage passwords, 2FA tokens, and permissions.
• AI-Assisted Problem Solving & QA: use AI thoughtfully with strict human oversight.
• Proactive Daily Reporting: provide daily asynchronous updates with priority statuses and blockers.
• Special Projects & Operational Support: support HR/finance/partners and prepare briefs.

Skills

Executive Assistant experience

English fluency

Security discipline

Systems thinking

AI fluency

Cloud tools proficiency

Tools

Google Workspace

Slack

Ramp

Job description

Insideoutva is seeking an Executive Assistant to be the right hand to our Founder & CEO. This remote role focuses on high-trust, precise calendar management, inbox handling, travel logistics, and day-to-day operations.

Ideal candidates have excellent English, impeccable organizational skills, and a disciplined approach to security and AI-assisted workflows, with experience supporting senior leaders in a fast-moving remote setting.